α-azidocinnamaldehyde | 820975-55-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: α-azidocinnamaldehyde
• 英文别名: 2-Azido-3-phenylprop-2-enal
• CAS: 820975-55-1
• 化学式: C₉H₇N₃O
• 分子量: 173.174
• InChiKey: KZTQGYGRVHCTMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-azidocinnamaldehyde 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.33h， 生成 ethyl 2-(4-benzoyl-1-(4-chlorophenyl)-2-phenoxy-1H-imidazol-5-yl)acetate
  参考文献：
  名称：

  通过连续的Aza-Wittig / Michael /异构化反应合成1,2,4,5-四取代的咪唑

  摘要：

  由亚氨基磷烷3与芳基异氰酸酯的氮杂-维蒂希反应获得的碳二亚胺4在催化量的醇钠存在下与仲胺反应，以高收率得到1,2,4,5-四取代的咪唑7。然而，由于预期产物10的进一步空气氧化，由于在催化量的碳酸钾的存在下使用苯酚，因此获得了4-酰基咪唑11。

  DOI：

  10.1021/jo201846w
• 作为产物：
  描述：

  α,β-dibromocinnamaldehyde 在 sodium azide 作用下， 生成 α-azidocinnamaldehyde
  参考文献：
  名称：

  New efficient synthesis of 1,2,4-trisubstituted imidazoles and imidazo[1,2-c]quinazolines by a tandem aza-Wittig/electrocyclic ring-closure process

  摘要：

  A series of 1,2,4-trisubstituted imidazoles 5 were synthesized efficiently by a tandem aza-Wittig/1,5-electrocyclic ring-closure reaction of vinyliminophosphoranes 3 with aldehydes. Reactions of 5s,t with triphenylphosphine produced iminophosphoranes 7. A tandem aza-Wittig reaction of iminophosphorane 7 with isocyanate generated imidazo[1,2-c]quinazolines 9 in high yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.005

文献信息

• A “one-pot” multicomponent approach to polysubstituted 4-aminopyridines
  作者：Jiaan Shao、Wanwan Yu、Zhanying Shao、Yongping Yu

  DOI：10.1039/c2cc17850h

  日期：——

  A novel and facile domino reaction has been developed to synthesize a variety of polysubstituted 4-aminopyridines from α-azidovinylketones, aldehydes and methylamine derivatives in reasonably good yields under mild conditions. Additionally, a possible mechanism is proposed.

  一种新颖且简便的多米诺反应已被开发，用于在温和条件下以合理良好的产率合成多种多取代的4-氨基吡啶，原料为α-叠氮乙烯基酮、醛和甲胺衍生物。此外，还提出了一种可能的机理。
• Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides
  作者：Na Liu、Fei Chao、Ming-Guo Liu、Nian-Yu Huang、Kun Zou、Long Wang

  DOI：10.1021/acs.joc.8b03242

  日期：2019.2.15

  This paper reports the tandem reaction strategy of the Passerini/Staudinger/aza-Wittig reaction based on the in situ capture of isocyanides. According to this strategy, isocyanides are synthesized in situ and immediately work as the substrate for the Passerini reaction and postmodification tandem reaction in one pot. In addition, two types of new compounds, 5-oxo-3,5-dihydrobenzo[e][1,4]oxazepines

  本文基于异氰酸酯的原位捕获，报道了Passerini / Staudinger / aza-Wittig反应的串联反应策略。根据这一策略，异氰化物可在原位合成，并立即用作一罐中Passerini反应和后修饰串联反应的底物。此外，还使用以下方法合成了两种新型化合物：5-氧代-3,5-二氢苯并[ e ] [1,4]氧氮杂卓和6-氧代-5,6-二氢-2 H -1,4-恶嗪。一站式反应策略，其中包括五步转化。
• One-Pot Synthesis of 2,4,5-Trisubstituted Oxazoles via a Tandem Passerini Three-Component Coupling/Staudinger/Aza-Wittig/Isomerization Reaction
  作者：Ming-Wu Ding、Long Wang、Zhi-Lin Ren、Min Chen

  DOI：10.1055/s-0033-1340596

  日期：——

  2,4,5-Trisubstituted oxazoles were prepared via a tandem Passerini three-component coupling/Staudinger/aza-Wittig/isomerization reaction in one-pot fashion, starting from easily accessible α-azidocinnamaldehyde s , acids, isocyanide and triphenylphosphine.

  2,4,5-三取代的恶唑是通过串联 Passerini 三组分偶联/施陶丁格/氮杂-维蒂希/异构化反应以一锅方式制备的，从容易获得的 α-叠氮基肉桂醛、酸、异氰化物和三苯基膦开始。
• Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones
  作者：Bao Hu、Zhao Wang、Ning Ai、Jie Zheng、Xing-Hai Liu、Shang Shan、Zhongwen Wang

  DOI：10.1021/ol202650z

  日期：2011.12.16

  A highly efficient and convenient method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles from readily accessible 2-azido acrylates and nitrones has been developed. This reaction proceeded under mild conditions without the assistance of any metal, acid, or base.

  已经开发了一种由容易获得的2-叠氮基丙烯酸酯和硝酮合成1,2,4,5-四取代的咪唑的高效便捷的方法。该反应在温和条件下进行，无需任何金属，酸或碱的辅助。
• Synthesis of poly-functionalized imidazoles via vinyl azides annulation
  作者：Jing Luo、Wenteng Chen、Jiaan Shao、Xingyu Liu、Ke Shu、Pai Tang、Yongping Yu

  DOI：10.1039/c5ra07320k

  日期：——

  An efficient annulation of vinyl azides with activated imines has been developed for the synthesis of poly-functionalized imidazole derivatives. This reaction includes thermal decomposition of vinyl azides to 2H-azirines, nucleophilic attack of 2H-azirines with activated imines and subsequent cyclization to desired imidazoles.

  已经开发了具有活化的亚胺的乙烯基叠氮化物的有效环合，用于合成多官能化的咪唑衍生物。该反应包括2个乙烯基叠氮化物的热分解ħ -azirines，2个亲核攻击ħ与活化亚胺和随后的环化，以期望的咪唑-azirines。